Cloud Systems Administrator Full Time

You will be responsible for administering and supporting a hybrid Microsoft collaboration environment, including Microsoft 365, Exchange (Online and hybrid), Microsoft Entra ID (Azure AD), and Microsoft Teams. As part of a team that builds and operates Penske’s enterprise collaboration and identity services, you will support the implementation, operation, and continuous improvement of secure, scalable messaging and collaboration platforms.

In this role, you will provide technical and operational support to IT teams, contribute to system documentation and implementation efforts, and assist with business continuity and disaster recovery readiness for Microsoft 365 services. You will collaborate with platform, network, and security teams to deliver reliable operations across identity, email, and collaboration services.

Location:

Corporate headquarters in Reading, PA or Tampa, FL.

Penske Responsibilities:

• Administer and support Microsoft 365 services in a hybrid environment (Exchange Online/Hybrid, Microsoft Entra ID, Teams, and third-party SaaS), including service health monitoring and response to incidents, advisories, and tenant changes.
• Collaborate with stakeholders (Service desk, Security, Networking, and Application teams) to implement Microsoft 365 solutions and continuously improve service performance and user experience.
• Provide operational support and troubleshooting for production Microsoft 365 services, including mail flow, client connectivity, Teams issues, and identity/authentication incidents.
• Manage Exchange Online and Exchange hybrid configuration, including connectors, transport rules, accepted domains, certificates, patching, and hybrid mail flow.
• Administer Microsoft Entra ID, including user lifecycle management, group and role-based access control, Conditional Access support, MFA troubleshooting, and integration with enterprise applications.
• Maintain availability and resilience by supporting backup/restore strategies where applicable, hybrid dependencies, and documented Disaster Recovery procedures for critical collaboration services.
• Coordinate changes and deployments with other IT teams and vendors, ensuring appropriate testing, communication, and post-change validation.
• Create and maintain operational documentation, knowledge articles, and technical diagrams/standards for M365, Exchange hybrid, Entra ID, and Teams.
• Support identity and access integrations for enterprise SaaS applications (e.g., Proofpoint), including directory synchronization, SSO/federation troubleshooting (SAML/OAuth), application registrations, and certificate and secret lifecycle management, in coordination with vendors and application owners.
• Support remediation and recovery activities including rollbacks, service restoration, and root-cause analysis, and assist in driving corrective actions to prevent recurrence.
• Other projects and tasks as assigned.

Penske Qualifications:

• Associate’s degree in Information Technology, Computer Engineering, or a related field preferred, or equivalent experience, including a minimum of 2 years of system engineering and IT support experience.
• 1+ year of hands-on experience administering Microsoft 365 services preferred, including Exchange Online, Microsoft Entra ID, and Microsoft Teams, with a focus on troubleshooting and operational support.
• Experience with Exchange hybrid environments preferred, including mail flow, connectors, certificates, Autodiscover, and directory synchronization dependencies.
• Working knowledge of identity and access management concepts, including authentication, authorization, MFA, and Conditional Access, with the ability to troubleshoot sign-in and access issues.
• Experience with automation and administration using PowerShell preferred, including Exchange Online, Microsoft Graph, and Microsoft Teams.

Understanding of enterprise networking fundamentals (DNS, TCP/IP, proxies, and firewalls) as they relate to Microsoft 365 connectivity and service reliability.

Physical Requirements:
The physical and mental demands described here are representative of those that must be met by an associate to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
The associate will be required to: read; communicate verbally and/or in written form; remember and analyze certain information; and remember and understand certain instructions or guidelines.
While performing the duties of this job, the associate may be required to stand, walk, and sit.
The associate is frequently required to use hands to touch, handle, and feel, and to reach with hands and arms. The associate must be able to occasionally lift and/or move up to 25lbs/12kg.
Specific vision abilities required by this job include close vision, distance vision, peripheral vision, depth perception and the ability to adjust focus.
This is a hybrid work environment, expectations are to be in the office in person at least two days a week. There may be occasion for collaboration days or requests from leadership to be present more than the two minimum.

Penske is an Equal Opportunity Employer

About Penske Truck Leasing/Transportation Solutions

Penske Truck Leasing/Transportation Solutions is a premier global transportation provider that delivers essential and innovative transportation, logistics and technology services to help companies and people move forward. With headquarters in Reading, PA, Penske and its associates are driven by a dedication to excellence and a commitment to customer success. Visit Go Penske to learn more.

Job Category: Information Technology

Job Function: Application Delivery & Support

Job Family: Information Technology

Address: 100 Gundy Drive

Primary Location: US-PA-Reading

Employer: Penske Truck Leasing Co., L.P.

Req ID: 2604394